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Chemical Structure| 503614-56-0

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Product Details of [ 503614-56-0 ]

CAS No. :503614-56-0
Formula : C16H17N3O4
M.W : 315.32
SMILES Code : CCOC(=O)C1=NN(C2=C1CCNC2=O)C1=CC=C(OC)C=C1
MDL No. :MFCD21340322
InChI Key :PSOYDCQSXGQZKM-UHFFFAOYSA-N
Pubchem ID :22240468

Safety of [ 503614-56-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 503614-56-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 503614-56-0 ]

[ 503614-56-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 545445-40-7 ]
  • [ 27143-07-3 ]
  • [ 503614-56-0 ]
YieldReaction ConditionsOperation in experiment
81.2% With N-ethyl-N,N-diisopropylamine; In ethyl acetate; at 85 - 95℃; for 20h;Inert atmosphere; Green chemistry; Under nitrogen atmosphere, ethyl acetate (360 mL) was added with 18.2 g of 5,6-dihydro-3-(4-morpholinyl)-2(1H)-pyridone andEthyl [(4-methoxyphenyl)hydrazino]chloroacetate 30.8 g, 19.4 g of diisopropylethylamine was added under stirring, and the reaction was heated to 85 to 95°C and stirred for 20 hours. After cooling to 15 to 25° C., 35 mL of trifluoroacetic acid was added dropwise after filtration, followed by stirring at 15 to 25° C. for 2 hours.Adding 10percent sodium bicarbonate solution to quench the mass percentage (the mass percentage refers to the percentage of sodium bicarbonate in the total mass of aqueous sodium bicarbonate, the same below), and then extracted with ethyl acetate 1 Times.The organic phase was washed with a 10percent by weight aqueous solution of sodium bicarbonate and a 15percent by weight saline solution (the mass percent containedThe amount refers to the percentage of sodium chloride in the total mass of the saline solution) and is dried over anhydrous sodium sulfate.Filtration and concentration in vacuo (45-55°C, -0.085 MPa--0.1 MPa) afforded a yellow solid.The yellow solid was added to 150 mL of ethyl acetate, heated to 75-85°C and stirred for 1 hour to dissolve, cooled to 0-5°C and stirred for 2 hours, filtered, washed with 0-5°C ethyl acetate, and dried at -0.01. Vacuum drying at MPa--0.1MPa, 45-55°C for 8 hours to 12 hours to obtain a pale yellow solid25.6 g, yield 81.2percent, HPLC purity 98.30percent.
At room temperature, compound D (for example, 4.7 mmol) and 3-morpholino -5,6-dihydro-pyridine -2 (1H)-one (for example, 0.94 g, 5.2 mmol) is added to the reaction flask (for example, 100 ml) in, then adding toluene (for example, 20 ml) and triethylamine. After the completion of the addition, the resulting mixture is heated to 100 °C, the reaction to reflux 12 hours. The resulting mixture to cool to room temperature, concentrated. To the residue add dichloromethane (for example, 20 ml), at room temperature the acid adds by drops trifluoroacetic acid (for example, 5.0 ml). The resulting stirring reaction mixture of 2 hours. After the completion of the reaction, the resulting mixture is concentrated under reduced pressure. After the completion of the concentration, to the resulting added in the mixture of ethyl acetate and purified water (appropriate amount). Stirring the resulting mixture, precipitated solid. Filtering the mixture obtained, the filter cake drying under reduced pressure, to obtain the product, yield by about 30percent.
  • 2
  • [ 27143-07-3 ]
  • [ 207976-92-9 ]
  • [ 503614-56-0 ]
YieldReaction ConditionsOperation in experiment
66.1% With triethylamine; In toluene; for 12h;Reflux; Under room temperature, the toluene (500 ml), 3-chloro -5,6-dihydro-pyridine -2 (1H)-one (35 g, crude), 2-chloro-2 - (2 - (4-methoxyphenyl) hydrazono) ethyl acetate (30.8 g, 0 . 120 mol) and triethylamine (24.2 g, 0 . 240 mol) are added to a reaction flask. The obtained mixture is heated to reflux under agitation, and the reaction to reflux 12 hours. The resultant mixture to cool to room temperature, into ethyl acetate (500 ml) and water (500 ml) in a mixed solution, filtered. The obtained filter cake drying under reduced pressure to get the yellow solid 25.0 g, that is, 1 - (4-methoxyphenyl) - 7-oxo -4, 5, 6, 7-tetrahydro -1H-pyrazolo [3,4-c] pyridine-3-carboxylic acid ethyl ester (yield: 66.1percent).
56% With triethylamine; In toluene; at 130℃; for 4h; General procedure: Toluene (1.55 dm3), 62 g 11 (0.471 mol), 242 g 3(0.943 mol), and 286 g triethylamine (2.828 mol) were sequentially charged at RT into a 3 dm3 three-neckedround-bottomed flask, fitted with a condenser, a mechanical stirrer, and a CaCl2 guard tube. The reaction mixture was refluxed at 130 °C for 4 h, cooled to RT, poured into930 cm3 ice cold water, and extracted with dichloromethane(4 9 930 cm3). The organic layers were combined, washed with brine (2 9 930 cm3), dried over anhydrous Na2SO4, and concentrated under reduced pressureat <55 °C. The crude material thus obtained was stirred with 620 cm3 MTBE for 1 h at RT, filtered, washedwith 310 cm3 MTBE, and finally dried at 45 C for 2 h toobtain 14 (83 g, 56percent, 99.3percent purity by HPLC analysis) as abrown solid. 1H NMR spectral data of 14 (see SupplementaryMaterial for details) was found to be consistent withthe values described in Ref. [15]
  • 3
  • [ 503614-56-0 ]
  • [ 1007-03-0 ]
  • ethyl 6-(4-(cyclopropylcarbonyl)phenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
43.8% With copper(l) iodide; 8-quinolinol; potassium carbonate; In dimethyl sulfoxide; at 140℃; for 4h; To a 25 mL two-necked round bottom flask was added 1- (4-methoxyphenyl) -7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3, 4-c] pyridine-3-carboxylate (0.502 g, 1.60 mmol), cyclopropyl (4-iodophenyl) methanone (0.43 g, 1.58 mmol), 8-hydroxyquinoline (70 mg, 0.48 mmol) (0.662 g, 4.8 mmol), cuprous iodide (91.44 mg, 0.48 mmol) and dimethylsulfoxide (15 mL) were added and the mixture was heated to 140 C for 4 hours.After cooling to 25 C, water (30 mL) was added and extracted with dichloromethane (20 mL x 2). The combined phases were washed with saturated brine (20 mL) and dried over anhydrous sodium sulfate.The crude product was purified by column chromatography (petroleum ether / ethyl acetate (v / v) = 1/2) to give a white solid (0.32 g, 43.8%).
  • 4
  • [ 27143-07-3 ]
  • [ 503614-56-0 ]
 

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